Cyclization of 4-Hydroxy-4-methyl-1-pentyl p-Toluenesulfonate as a Model to Evaluate Inherent Medium Effect on SN2 Solvolysis

Article abstract of DOI:10.1246/cl.1991.2065

Solvent effect on the cyclization of 4-hydroxy-4-methyl-1-pentyl p-toluenesulfonate, a mechanistic equivalent to the S_N2 solvolysis, was successfully analyzed by Taft LSER equation as log k=3.2?^*+1.4α+1.9β-8.36, indicating that three independent factors are operative, i.e., solvent polarity and H-bond donor ability which promote ionization, and H-bond acceptor ability which enhances nucleophilicity of the internal OH group.